Love is a Complicated Business
by RosesandThorns666
Summary: AU. Dean Winchester and Chrissie Singer are good friends, and during a weekend stay with their friends they grow closer. Dean has to try to cope with falling in love for the first time along with the usual high school drama. Please R&R!
1. Whispers in the Dark

**Summary: **AU. Dean Winchester and Chrissie Singer are good friends, and during a weekend stay with their friends they grow closer. Dean has to try to cope with falling in love for the first time along with the usual high school drama. Please R&R!

**Disclaimer: **I don't own _Supernatural _or its characters. I only own Chrissie Singer.

**A/N: **Damn! This chapter is such a long opener! The others may not be as long as this, but they'll be at least 2000 words hopefully.

I'd like to thank **_luckypixi _**for helping me with the title!

Hope you enjoy!

xxxxxxxxxxxxxxxxxxxxx

**

* * *

Love is a Complicated Business**

**~Chapter One: Whispers in the Dark~ **

Chrissie had just lost her mother. Times were hard for both her and her father, Bobby, the two of them now standing at Karen's grave. Bobby's arms were around his daughter as she sobbed into his chest, Bobby running his fingers through her auburn curls to calm her whilst crying himself. The service ended and father and daughter shared a hug and a kiss on the cheek before turning to their friends.

Chrissie's beautiful brown eyes met Dean Winchester's green ones, a weak almost-smile crossing her full lips as she stepped towards him, her friend winding gentle arms around her before their other friends joined in the hug.

They were all there for her, Sam (Dean's little brother), Jess, Anna, Crowley, Gabriel, Jo, Chuck, Castiel, Jimmy, Becky and even Jo's cousin, Ash.

"We're so sorry, Chrissie," Becky whispered, sharing her own hug with the young girl, "We're sorry."

"Thanks for being here, guys." Chrissie breathed, sniffling and dabbing her eyes as she and the others set off towards their cars.

They headed to Bobby's for the wake, Chrissie spending the afternoon being shown sympathy and care from all her friends, Dean being the last to leave.

"See you at school on Monday," Chrissie said softly, hugging Dean and kissing his cheek, "Thanks for being with me today..."

"Anytime." Dean replied, "See you Monday."

He turned to leave, really not wanting to go anywhere, but Chrissie and her father needed their time alone. Dean's parents and Chrissie's parents had been really good friends, as they had been with Jo's parents. The three of them, and of course, Ash, had grown up together, their other friends coming into their lives in elementary school. They'd all been close since, and now, Sam and Jess were dating in their first relationship, Becky and Chuck were together, as were Crowley and Jo, and Anna and Gabriel.

Everyone wanted Dean and Chrissie to be together, but it just wasn't happening. The two of them were too chicken to admit their feelings to each other, which pissed everyone off, but Crowley had come up with a plan to try and get them together set for the following weekend. It would bring Dean and Chrissie closer, and get Chrissie out of the house. She'd need her own time, as her father would after her mother's tragic death. Karen had died in a car accident, dying instantly, much to Bobby and Chrissie's relief. They'd rather her have died instantly than have her be in a hospital suffering through a long painful death.

* * *

"So, my parents are away for a week, and I have that enormous house to myself," Crowley said, Jo chuckling and snuggling up to her boyfriend.

They were all in the dining hall at school, the huge group of them sitting on one table which normally pissed others off, but they should get to a table first if they want it.

"I sense the word 'Party' drifting through the air." She said, Crowley licking his lips and nodding.

"With booze." He said, "And ghost stories about the place, and music, and dancing...and sex."

With that he turned to look at Jo who blushed and kissed his cheek, biting her lip and smiling.

"Okay." She said, "I'm up for it."

"Me too." Dean added.

"Sam and Jess are more than welcome too if you want to ask them." Crowley said with a smile, Dean nodding in response, "But obviously for them...no sex...or booze..."

"Sounds like my kinda party." Ash laughed.

"Yeah, we'll come too." Jimmy said, throwing an arm around his twin brother who sighed and rolled his eyes, "We'll tell Gabe."

"We're up for it too." Chuck laughed, Becky smiling and kissing his cheek.

"And me." Anna added, turning to the final member of the group, "Chrissie?"

"Um..." Chrissie began, "Gee...I dunno, um...my dad kinda needs me at the moment...you know, since we lost my mom and all..."

"Chrissie, you need to get out of the house, love." Crowley said, "Your dad'll probably tell you it's good for you."

"Well, I'll run it by him first." Chrissie replied, "I'll let you know tomorrow."

The others nodded and Chrissie gazed out of the window, her index finger running under her bottom lip and back as she thought. She did miss her mother, but would it be so selfish to try and get out of the house and have a little fun? She'd check with her dad.

"Who's up for going outside?" Jo asked, everyone nodding and getting up, slinging their bags over their shoulders while Dean checked on Chrissie.

She looked so beautiful today, he thought, dressed in dark blue jeans and black tank top, her purple checkered shirt over the top and open, her white and blue sneakers on her feet and hair tied in a ponytail over her shoulder. Her full lips were glittered with a soft layer of lip gloss, no mascara on her eyes which was unusual. She probably hadn't put any on in case she cried. The poor kid had just buried her mother, she and her dad being the only members left of the Singer family.

"Chrissie?" He asked, "You okay?"

The young girl smiled up at him and nodded, slinging her bag over her shoulder and linking arms with her childhood friend and heading out into the yard with him. Chrissie liked Dean. He was always there for her. He was sweet, caring and kind, but all of that was hidden beneath that manly façade of his. He was a strong, brave young man; not one for chick-flick moments, as he called them, but he always had a soft spot for Chrissie. He didn't think the others had noticed but it was obvious to them. He was the one she'd turned to through all her pain and all her troubles, and he'd done the same to her. This weekend would be good for her, but after a few drinks, he knew he'd barely be able to keep his hands off of her.

* * *

Crowley's house was a truly beautiful place. It was a large stone mansion, the largest in the city, and he had all these spare rooms to himself. His parents only used a few of the rooms and he was confused as to why the place had so many, but at least when he had a party, his friends could all have their own room and bathroom for the night. Chrissie made her way up the steps outside, texting her dad to let her know she was there, her bag over her shoulder as she was graced with Crowley at the door, a whiskey in his hand.

"Hello, darling." He said, the British accent making Chrissie smile as usual.

"Hey, sweetheart." She replied, kissing Crowley's cheek and hugging him, "You okay?"

"I'm fine," Crowley replied, "You alright?"

"I'm okay."

Within the hour, Chrissie was drunk enough to get up and dance with Becky and Crowley to _Only Girl in the World_. Quite why Crowley was dancing to that was a mystery to the others, but he, Becky and Chrissie were having fun and making the others laugh. Dean watched Chrissie's smile, taking in how gorgeous it was. It was much better than her crying or looking as down as she had over the past couple of weeks, but it's hardly surprising since she and her mother were so close. Everyone had been paired off into rooms, Crowley pairing Dean and Chrissie together, neither of them noticing his plan. The pair of them really were quite dense about how in love with each other they were. Any idiot could see it.

Castiel had a trick of his own up his sleeve. He tapped Jimmy on the arm, whispering something to his twin who nodded and changed the song to _Every Time we Touch. _Trust him. Crowley called Jo, a very drunken Ash grabbed Castiel, Anna grabbed Gabriel and Becky called Chuck while Sam led Jess for a dance. Jimmy looked over at Dean who gazed at Chrissie, the young girl looking a little dejected as she moved out of the way of the others.

"Dude," Jimmy began, "Take her for a dance."

Dean looked up at Jimmy and raised an eyebrow.

"Look at her..." Jimmy said, "She looks so alone, go and dance with her, dude!"

Dean sighed, putting his beer down before getting up, seeing Chrissie actually heading towards the hallway with her coat over her arm. He got to her just in time, taking her wrist gently and pulling her towards him.

"Come and dance with me, huh?" He said, Chrissie nodding sadly before putting her coat back over the arm of one of the sofas and sliding her hand into Dean's, "Atta girl."

Dean wasn't a slow-dancer but for Chrissie he'd do anything. He took her into his arms and they danced slowly, the young girl winding her arms around his neck and resting her head on his shoulder, Dean holding her around her upper and lower back, pressing his cheek to her forehead to let her know he was there for her. He'd always be there for her, no matter what. He wanted to be with her so much, but he just couldn't tell her, especially not since her mother had just died.

"Don't go home tonight," He whispered to her, "Stay with us, huh?"

He felt a gentle nod against his shoulder and he smiled.

"You know we're all here for you, right?"

"Thank you."

* * *

"Okay," Crowley slurred, "King-sized bed in here...plenty of room for you to fuck..."

Dean rolled his eyes.

"Alright, Crowley, you'd better get back to Jo." Dean said, "Thanks for showing us the room! Bye!"

With that he closed the door, Chrissie giggling at the annoyed sound Crowley made before hearing his call for Jo to 'shake a leg, woman!'. She put her bag on the bed, taking out her white vest top and blue pyjama bottoms, smiling at Dean before heading to the bathroom to get changed. Dean, now that Chrissie wasn't in the room, unfastened his jeans and let them drop, stepping out of them and taking off his shirt, slipping on his sweatpants and folding his clothes up.

He turned to see Chrissie leaving the bathroom in her pyjamas, beautiful auburn curls hanging over her shoulders as she brushed them. Chrissie was met with Dean. Her Dean. Her shirtless, fucking gorgeous Dean. Well...she wished he was her Dean, but she didn't think he ever would be. He treated her like a baby sister rather than a lover and that fact saddened her so much. She didn't want to feel sad anymore.

"Hi." Dean said, Chrissie smiling at him and giggling softly.

"Hi." She replied, moving over to her bag, "I got somethin' a little extra. It didn't get used downstairs so I guess you and I could share it?"

She pulled out a bottle of whiskey and Dean smiled, sitting on the bed with his t-shirt still in his hands.

"Are...are you okay with me sleeping like this or...?" Dean began awkwardly, Chrissie knowing what he meant and raising a hand.

"It's fine, sweetie, don't worry about it." She said, "It's hot in here anyway."

Was it hot in the room or was it just her?

She pulled out two of her many shot glasses she'd packed into her bag and smiled before putting her clothes and other stuff away, her bag going on the floor by the foot of the bed. They got under the sheets, Dean checking his phone to see it was twelve-forty in the morning. There was plenty of space between them, which was good because Dean was struggling to not touch her and hold her, to not lean forward and press his lips to hers. She wouldn't want a boy like him, one who couldn't show how he truly felt because he was scared about what others would say. That made him feel pathetic and weak, but it was true.

"You want?" She asked, pouring her own whiskey.

"Thanks." Dean replied, Chrissie pouring him a glass and handing it to him, "Great party, huh?"

"Yeah." She replied, turning her head as the rain began to hit the windows of the bedroom they were in, "Wow...sounds pretty heavy..."

"Yeah." Dean said, taking the shot down and putting his glass on the bedside table, anything to calm his nerves.

Chrissie took down her shot too and lay back against the pillows, letting out a gentle sigh as her thoughts wandered to her mother.

"You wanna hear something funny?" She asked, turning on her side to look at Dean.

"Okay." Dean replied, turning on his side to look at her too.

"The other morning," Chrissie said, the lump beginning to appear in her throat, "I came downstairs and I asked my dad where Mom was."

Dean looked at her, confused as to why that was funny. It wasn't, and Chrissie knew it wasn't, but Dean knew she'd just said that so she could get it off her chest. She had a lot of stress and upset inside her still over her mother and knowing she'd done that would've made her feel a million times worse. The older teen grimaced as tears formed in her eyes, turning onto his back as Chrissie joined him, resting on his chest.

"Hold me..."

Dean was a little uncertain that this was a good idea. This could send Chrissie a confusing message, but she needed him so he wound his arms around her, feeling hers resting on his chest, her left sliding under his right arm to hold his shoulder. He felt her tears hitting his body and he closed his eyes, unable to suppress the need to kiss her forehead. And he did, tenderly and gently, seeing her look up from his shoulder and gaze into his eyes. They just looked at each other, from eyes to lips and back before Chrissie leaned forward a little, pressing her lips to Dean's.

To say that Dean was surprised was an understatement. Chrissie was kissing him! His Chrissie who he'd waited a long time for was now in his arms, sharing a bed with him and was kissing him. He kissed back, a little unsure, which was uncommon for Dean Winchester, finding the kiss growing deeper. When it was broken, the pair just looked at each other, both a little wide-eyed before they settled, their gazes soft and tender as they looked at each other.

"Dean?" Chrissie asked, feeling Dean's hold on her tighten a little, "What does all this mean?"

"You mean the kissing and the...the cuddling?" Dean countered, earning a nod, "Um...I...I know I wanna be with you..."

The first genuine smile that Dean had seen on Chrissie for almost three weeks shone through and he knew that this was what she wanted too. He didn't know if it would be anything serious but deep in his heart he knew he wanted it to be.

"I wanna be with you too..."

The new found lovers kissed again, thunder coming from outside and lightning's flashes making Chrissie jump and break the kiss. She looked to the window, turning out her lamp while Dean turned out his and rolled onto her side away from him, facing the window. Dean turned over too, winding a protective arm around her waist and feeling her take his hand gently in her own. He kissed her temple and then her cheek, unafraid to snuggle down with her and hold her close to him, reassuring her that he was still here.

"Night, Chrissie."

"Goodnight, Dean."

-TBC-


	2. After a Hurricaine Comes a Rainbow

**Summary: **AU. Dean Winchester and Chrissie Singer are good friends, and during a weekend stay with their friends they grow closer. Dean has to try to cope with falling in love for the first time along with the usual high school drama. Please R&R!

**Disclaimer: **I don't own _Supernatural _or its characters. I only own Chrissie Singer.

**

* * *

Love is a Complicated Business**

**~Chapter Two: After a Hurricaine Comes a Rainbow~ **

Chrissie awoke the next day, which thankfully was Saturday, to feel gentle fingers in her hair, unsure of where she was until she saw her shot glass on the bedside table. She sighed, leaning into the touch of whoever was stroking her hair. Then she remembered. _Her Dean_.

"Dean?"

"Hey," Dean whispered, "Mornin', Chrissie."

"Morning, Dean." Chrissie replied, rolling over and kissing Dean's lips gently.

Dean deepened the kiss, both of them jumping apart as they heard footsteps along the corridor.

"Wakey, wakey, darlings!" Crowley called from the other side of the door, a groan of pain coming from him after, "Get up, breakfast time!"

The footsteps faded as Crowley went to Chuck and Becky's room, calling them awake too, groaning in pain again.

"He's hung over." Dean laughed, turning to see Chrissie sat up with her vest top gone, white lace bra remaining, "Jesus, I'm sorry..."

"No, it's okay," Chrissie said sweetly, "We're a couple now...you're allowed to look, y'know."

Dean looked sheepishly and saw his girlfriend giggle, her dainty hand coming up to stroke his face.

"You cute little idjit." She said with a smile, leaning forward and taking Dean's hands, "We're not fourteen and havin' a fumble behind the bikesheds."

Dean couldn't hide his smile and he kissed her lips, feeling her press close to him.

"We'd better go if we want some food...you know what Chuck and Jimmy are like." She said, Dean laughing in response before climbing out of bed, the two of them getting dressed with their backs to each other before quickly freshening up and sharing a sweet kiss.

"What do we tell them?" Dean asked, "You wanna tell the others?"

Chrissie bit her lip and rubbed her forehead.

"You're serious...about wanting to be with me, I mean?"

"Of course." Dean replied, "I wouldn't lie to you about that, Chrissie."

With that, he looked deep into her eyes before kissing her deeply, pulling her close to him and pressing his forehead to hers.

"I really care about you..." Dean said, "And I'd never hurt you, baby."

Baby. The pet name sent shivers running down Chrissie's spine. She never thought that Dean would call her _baby _ever, and yet here he was on a bright Saturday morning calling her _baby_. She was his girlfriend now. He was her boyfriend, and she was prepared to show the whole world that finally she had the man she'd waited for, for so long. Maybe they were just eighteen, but Chrissie felt something so deep for Dean it began to frighten her, but it wouldn't stop her being with him.

"Okay. Let's tell 'em." She said, taking Dean's hand as they headed out of the room.

They walked down the corridor, bare feet silent against the wooden floor as they made their way to the stairs, fingers locked while Dean's thumb stroked over Chrissie's gently. They were both nervous about revealing their relationship, hoping their friends would understand. Like they wouldn't! They were all with each other anyway, and plus, unbeknownst to the couple, this is what they'd wanted. How could they not be understanding? There they all sat at the large table near the bottom of the stairs, glasses of water and slices of toast on plates before them.

"Morning, guys." Dean said, everyone looking up as he and Chrissie made their way down the stone stairs, everyone gasping when their entwined fingers came into view, "Great party last night, Crowley."

"Thanks, Dean." Crowley said, "Busy last night were we?"

He gestured to their hands and Chrissie blushed, Dean chuckling in response.

"Not _that _kinda busy, pervert." Dean said, "But yeah, Chrissie and I are together so you can all close your mouths before you catch flies."

"WE NEED DETAILS!" Becky screeched, frightening the crap out of Chrissie before the poor girl was grabbed by Becky, Anna, Jo and Jess, all of them dragging her into another room.

"So what happened?" Anna asked, "Did he confess his undying love for you and bend you backwards like guys do in the old movies?"

"Did he fuck you senseless?" Becky asked.

"DID HE PROPOSE?" Jess screeched, the others looking at the girl as though she'd grown a second head.

"No!" Chrissie said, trying to keep them quiet so Dean wouldn't hear, "We were just talking...and I told him something about my mom...I started crying and asked him to hold me, which he did and we ended up kissing...twice..."

"Awww!" The others cried.

"That's so adorable!" Becky sighed.

"Sweet, completely sweet," Anna chuckled, "So...there wasn't any nakedness?"

"He was bare-chested," Chrissie replied, "But he was like that before we even got into bed, so..."

"Is his body nice?" Jess asked.

"Beautiful." Chrissie replied, "Toned and tanned...and unblemished."

She sighed dreamily and the girls all squealed with delight.

"Ladies!" Crowley called, "We've got breakfast going cold out here!"

"Coming!" Jo called back, "We're coming, sweetheart!"

The girls returned to the other room, sitting by their partners and enjoying their breakfast. No-one missed the way Dean and Chrissie sat holding hands, their eyes barely leaving each other's as they ate. Crowley tutted, deciding to create a distraction.

"So..." He began, "Who got laid last night?"

Most of the table choked on their toast, the girls blushing while the boys coughed up their breakfast, Dean and Chrissie looking around at all the embarrassed faces.

"That makes us all then." Crowley said, "Well...apart from you two."

Chrissie laughed and Dean kissed her cheek, the young girl laughing like a maniac at the others, her first proper laugh in the time since her mother died. It was a lovely sound, one that all of them wanted to hear more often.

"What are we gonna do today, dude?" Chuck asked, recovering from his choking fit, "We got all day doin' fuck all!"

"Hey, Bassey, just stop for a minute," Crowley said, everyone chuckling at the nickname, "I've got ideas, okay?"

Chuck was nicknamed Bassey because his surname was Shurley, and Crowley had just thought of Shirley Bassey at the time. It just kind of stuck to the smaller teen, so everyone called him Bassey from then on.

"Come on then," Sam chuckled, "What do you suggest, oh mighty one?"

"Well, tonight we've got more alcohol and partying." Crowley said, "That's sorted, but I've got the swimming pool, the music room, the huge TV, a house big enough to play Hide and Seek in, plenty of places for Seven Minutes in Heaven and also enough spare bottles to play Spin the Bottle with."

Everyone exchanged glances.

"It's a good job we all packed swimwear then." Jimmy laughed, "I'm up for the pool."

The others all nodded and Crowley grinned, finishing his toast before grabbing all the plates.

"I'll deal with those later." He said, "First things third, we'd better clear up the living room from last night."

That was Crowley's favourite saying, first things third. He hated first things first and pointed out what a stupid phrase it was, coming up with first things third which everyone had laughed at. He was quick witted, like Gabriel and Dean, coming up with a lot of things that made the others laugh.

"Right, Jelly Beans." Gabriel said with a stretch, "I wanna get in that pool so let's shift our asses and clean up that living room."

* * *

Crowley and Jo were doing something gross in the shallow part of the pool, every assuming by the expression on Jo's face that they were fucking, whilst the twins were with Dean and Chuck and Becky were with Chrissie.

"What are you doing?" Castiel asked, "Go and be with her, Dean."

"Yeah, you're behaving like a nervous fourteen year old!" Jimmy laughed, "What's up?"

"I dunno," Dean replied, "I just don't wanna seem like I'm desperate and can't keep my hands off of her, y'know."

"You're playing the keep 'em keen game?" Jimmy asked, "Dude, grow up and go and spend time with her, okay? You guys haven't even looked at each other since breakfast, and that was two hours ago, what's going on?"

"I don't wanna make her uncomfortable either," Dean said, really shocked at what a baby he sounded, "Look, she's been through a lot over the past couple of weeks, and the last thing she wants is to be smothered by me, okay?"

"No, it's not okay." Castiel said, "She probably needs you to shower her with affection, you know, to show her you care. Go and at least talk to the girl, Dean."

Dean nodded and made his way over, wrapping his arms around Chrissie from behind and kissing her cheek.

"Hey, gorgeous." He whispered, Becky beaming at the couple and kissing Chuck's lips.

"We'll give you guys some time." Chuck said softly, he and Becky swimming to join the twins whilst keeping an eye on the couple who were sharing a gentle kiss.

"Dean," Chrissie began, "We've not spoken since this morning, and I hope you don't think that I was ignoring you or anything..."

"No, no, no," Dean said softly, Chrissie turning in his arms and kissing his lips lightly, "I know you weren't. It's okay, you've been through a lot recently."

"Yeah, but remember that song, _Firework_? Y'know, after a hurricaine comes a rainbow?" She began, Dean nodding in response, "Dean...you're my rainbow..."

Wow. Dean just stopped breathing for a moment, gazing at the young girl before him and seeing the tears forming in her eyes. He leaned forward and kissed her deeply, pulling into her embrace and holding her tightly. He sighed and pressed kisses to her wet hair, pulling back for them both to share passionate and deep kisses. He had no idea he had an impact like that on her. He didn't realise he meant so much to her and his world just seemed to grow brighter.

"Ah, look at the big girl." Gabriel chuckled, winding his arms around Anna who pressed into her boyfriend's embrace, the two of them watching from the other side of the pool.

If you were dating a Novak, you were hot to trot. The kids at school all remember Lucifer and Michael, and what legends they were in football and baseball, their shirts and trophies on display in the school's hall for all to see. Anna Milton had been dating Gabriel for three years, and despite the fact that his surname gave her more popularity, she loved him for _him_. She loved his cheekiness, his cute grin, his eyes, his hair, his sense of humour, his taste in candy and how much he loved her.

Gabriel loved her more than anything, and she knew it all too well. She loved him more than anything too, and her parents had finally gotten past the fact that Anna had found someone and to stop picking out his faults, as they always had. They did it to all of Anna's male friends until they accepted that Anna would spend time with them regardless, and quite why she didn't know. Gabriel had always called her father Jack behind his back, like Jack Burns on _Meet the Parents _and _Meet the Fockers_, both of them very alike in personality. Well...Anna's father wasn't as much of an asshole.

"Leave him alone!" Anna protested, "I think it's sweet."

"Oh God!" came Jo's strangled cry from the other side of the pool, everyone turning and watching with slightly disgusted expressions as she and Crowley reached climax.

"That's it!" Becky cried with disgust, "I'm outta here, you guys are sick!"

"What?" Crowley asked, "Can you blame me, really, when I'm with a girl as sexy as Jo?"

"That's so disgusting." Castiel breathed, ignoring Ash's laughter.

"WOOO! Go Crowley, go Crowley!"

"Ash, that's your cousin." Jimmy said, Ash's smile dropping as he climbed out of the pool with the others.

* * *

That night, the fire was burning bright in the large living room, Crowley and Jo curled up together in one armchair, Gabriel and Anna on a sofa, Dean and Chrissie on another and Sam and Jess in another chair. Castiel and Jimmy sat by the fire while Ash just snored loudly in the middle of the floor. There were soppy love songs playing through the room and everyone lay in comfortable silence.

"You okay?" Dean whispered, Chrissie nodding as she watched the flames burning brightly in the fire, "You sure?"

Chrissie wasn't okay. Everyone else could see it, and they could see the fact that the poor girl had tears streaming down her face.

"Chrissie?"

Chrissie pushed out of Dean's arms and made for the stairs, Dean jumping to follow her.

"Leave me alone!" She said, Dean stopping dead in his tracks and staring as she ran out of the room and up the stairs.

"Dean..." Gabriel breathed, "Don't just stand there! Go after her!"

Dean didn't know whether to leave her or not, but he went with his heart and he chased her to their room, knocking on the door gently.

"Please...let me in..." He whispered, "Baby, I can't settle if I know you're upset..."

There was a sniffle and then gentle footsteps, the bedroom door opening to reveal a tearful Chrissie.

"Dean..." She sobbed, "I'm so sorry..."

Dean took her hand and entered the room, locking the door behind him to hold her close to him, letting her cry out all her stress and fear against him.

"It's okay," He promised, "It's all gonna be okay, Chrissie..."

With each sob that escaped her lips, Dean felt a jolt of pain shoot through his body. He hated to hear her so distraught, and he kept her close, leading her to the bed where they lay down together, their fingers entwined and their bodies close. Chrissie's face became buried in Dean's neck, his strong arms holding her tightly to him, his gentle lips kissing her head and his tender fingers stroking her hair soothingly, hands rubbing her body as she shivered in his embrace.

He knew his relationship with Chrissie would require a lot of what he was providing now. She needed his care and his affection, his protection and his warmth. She needed his friendship, his bravery, his kind words and tender touches. And in all honesty, there were times when Dean needed the same from her, and she'd always provided what he'd needed. Now it was his turn to provide for her.

They fell asleep that night, tears still falling from Chrissie's eyes as she slept. She feared she'd never get over her mother, that she'd be stuck in this grief forever and that her dad would be too. She'd never seen her dad so isolated and so pained before and it was killing her to see him in so much suffering. But she had her Dean. Her Dean would be there to look after her and to help, he'd be there to protect her and to keep her safe, to hold her, to dry her tears and to support her, because he was her Dean. Her Dean protected everyone he could, he took out the time to care for others and in ways he was a hero to her.

She slept in the arms of her Dean, and she never wanted him to let her go.

-TBC-


	3. Too Much To Handle

**Summary: **AU. Dean Winchester and Chrissie Singer are good friends, and during a weekend stay with their friends they grow closer. Dean has to try to cope with falling in love for the first time along with the usual high school drama. Please R&R!

**Disclaimer: **I don't own _Supernatural _or its characters. I only own Chrissie Singer.

**A/N: **God, it feels like forever since I updated this! I started writing it and my motivation went, but I've made myself tear up with the majority of the writing in this chapter.

Hope you enjoy!

xxxxxxxxxxxxx

* * *

**Love is a Complicated Business**

**~Chapter Three: Too Much To Handle~ **

People gasped as Dean walked through the gates with Chrissie's hand in his own. The older teen smiled at his girlfriend and she pressed a kiss to his shoulder, Dean slinging his arm around her and Chrissie winding hers around his waist.

"Oh my God..." the cheerleaders breathed, muttering to each other and whispering as Chrissie and Dean walked by.

"Jealous bitches." Dean mumbled under his breath, smirking before stopping and pulling Chrissie close, kissing her passionately which left her breathless and the cheerleaders utterly stunned, "You're so gorgeous..."

"So are you." Chrissie blushed, smiling as the bell rang for class, "Oh, Dean...it's Biology..."

Dean grinned. They sat next to each other in most classes, but Biology was the class where they could get away with holding hands under the desk. He was worried though. When she'd gone home on the Sunday he'd texted her and called her, but she'd not answered or replied. If she did reply it was with simple one word answers, and at first he was worried that he'd done something wrong, but he knew that she was probably spending quality time with her father. Those two needed each other so badly at a time like the one they were going through now.

* * *

Their biology teacher was Miss Blake, who at times was a little slow or had what the kids would call blonde-moments. She was pretty forgetful at times, and the class was learning about natural processes involving micro-organisms...including decomposition of flesh. Dean felt Chrissie's grip on his hand tighten, and he tried to get the teacher's attention before Chrissie got too upset.

"And, for instance, if a body is buried, then creatures in the ground take the opportunity to feed."

Chrissie felt sick to her stomach, she tried to block out the words but before she knew it the tears were spilling down her face. All she could see was her mother in that coffin as she'd seen her on the day of the funeral. It was hard enough dealing with the concept that her mother was in a hole in the cold ground, in a white coffin all on her own, but now...

Miss Blake realised what she'd said and she covered her mouth, looking to Chrissie who was sobbing silently in her seat.

"Oh, Chrissie...I'm so sorry..."

Chrissie just bolted, Dean shooting up after her and Miss Blake flushing with guilt before promising her class she'd be back in a moment.

"Baby, it's okay..." She heard Dean whisper, exiting the room to find Chrissie in Dean's arms, Dean trying to console her the best he could.

"Chrissie?" Miss Blake asked, "Chrissie, I'm sorry...I completely forgot...I..."

"It's alright, Ma'am." Chrissie cried, "It's okay, I just overreacted, I'm sorry..."

"No, no, no, you didn't." The teacher replied, "I was just...I forgot. It's my fault, I'm sorry..."

"I'll be okay, Ma'am." Chrissie told her, Miss Blake shaking her head.

"Dean, would you take her to the library?" She asked, "Get your things and just take her out of the way to calm her...I'll write you guys a note..."

She headed back inside, Dean going in to get their things only to face his classmates, their friends looking concerned while the Masters siblings at the back of the room, (two of the quads on either side) spat insults and bitchy comments at him.

"Awww...poor little bitch missing her mommy?" Lilith hissed, gasping as Jo, who sat next to her, stabbed her with her pen.

"Shut up, whore." She spat, Crowley squeezing her hand while Alistair glared at him.

Crowley returned it and raised a challenging eyebrow, almost daring the younger boy to do something. Jo was grateful that her boyfriend was one of the toughest kids in school. No-one fucked around with Crowley. It was like an unwritten law.

You just did not fuck around with Crowley, not if you wanted to be able to walk by the time you'd finished with him. Some kids who were taller and stronger than him had run away from him screaming like girls. Alistair backed down, pulling Lilith closer to him while Jo squeezed Crowley's hand in thanks, earning her a gentle kiss to her temple.

"Here." Miss Blake said softly, "Again, I'm so sorry..."

"Miss Blake, it's fine." Dean said, "Just...Chrissie's gonna feel bad if you keep going on about it. She understands that not everyone can remember everything that happens to her, it's okay."

Miss Blake nodded, watching as Dean left the room with their things and sighing before turning to Lilith.

"Lilith Masters, if I ever hear anything as disgusting come out of your mouth again in my lesson, I will ensure that you are in detention for a month." She growled, "Am I clear?"

"Yes, Ma'am." Lilith replied, ducking her head and giving Miss Blake the finger as she turned away.

"Put your finger away, Lilith." Miss Blake said, Jo biting her lip to fight back a chuckle as Crowley did.

"Ah, the hell-whore got what she deserved." Crowley whispered, biting Jo's ear gently before continuing to listen to Miss Blake, he and the rest of his friends unable to stop worrying about Chrissie.

* * *

"It's just...knowing I go to a warm bed every night whereas my mother's in a wooden box in the ground...I feel so guilty..." Chrissie whispered tearfully.

She and Dean were tucked away in a corner of the library, her with her back to the large space so that people wouldn't see her upset.

"Baby..." Dean breathed, reaching out and taking her hand, "Your mom wouldn't want you to feel guilty."

Those words made Chrissie cry harder and Dean bit his lip, moving towards her and sitting by her side, pulling her close to him only for her to turn and embrace him, sobbing into his shoulder.

"Sweetie...I...I think you should go home...you're in no fit state to..."

"I'm okay, Dean." Chrissie sobbed, Dean shaking his head.

"Chrissie, you're...you're a mess..." He said, watching as hurt spread over her eyes.

"Thanks." She snapped.

"I didn't...you know what I meant." He told her, "You're breaking, Chrissie...you need some time to recover, okay? This isn't good for your mind to be so wrapped up in everything that's happening. Clearly you're still way too upset about this to be here."

"What are you saying? You wanna break up with me, 'cause it's something I'm too wrapped up in?" She asked, Dean grimacing and shaking his head.

"Baby, you know I didn't mean that. Stop twisting my words, okay?" He said softly, "If...no-one's gonna judge you for going home if you need to. You said yourself that you dad didn't want you here today."

Chrissie looked up at him with such guilt in her eyes that it hurt him to see.

"Chrissie..."

"I'm so sorry..." She whispered, "I'm...I'm taking this out on you and I shouldn't! I'm a horrible girlfriend. I'm horrible, I don't know why you'd want to be with someone who treats you like this..."

"Sweetie, you're not horrible..." Dean said, "You've been through one of the most traumatic things someone could ever go through, and I know you're so tired. You've not slept, Chrissie...not properly since Karen died...please, just...get yourself home and get some sleep."

"But..."

"Chrissie..."

Chrissie bit her lip and nodded, Dean kissing her gently and holding her close.

"You wanna go and see the principal?"

The young girl nodded and the two headed off to the principal's office, their fingers linked the entire way.

* * *

"Baby...?" Bobby whispered as he entered Chrissie's room, finding her in tears on her bed, "Sweetie, y'alright?"

"Daddy...?"

Her voice was so broken, so weak and small that Bobby's heart broke all over again. He bit his lip as tears filled his eyes, going to sit by his child who he still saw as that beautiful baby who'd been born eighteen years before, pulling her into his arms and rocking her as she sobbed and hiccuped in his arms.

"It's gonna be okay, Chrissie." He promised, "I know it hurts, but if we're strong...it'll pass gradually and we'll begin to move on. Your mother wouldn't want us to be so upset. She'd want us to carry on with our lives and she'd want us to be happy."

"But it's so hard!" Chrissie cried, almost hysterically as she sobbed in her father's arms, "I c-can't do it, Daddy, I can't!"

"Shhh..." Bobby soothed, "It's alright, you can do this. I'm with you, Dean's with you and all your friends are with you, okay?"

"I love you, D-Daddy..."

"I love you too, baby."

Bobby could hear someone knocking at the door downstairs, so he regained control of himself and kissed his child's head before leaving the room and going downstairs. He opened the door and was met with Dean who held a beautiful bouquet of flowers in his hand, one that Bobby guessed cost the boy a lot of money.

"Hi, Bobby." He said softly, "Is...is Chrissie in?"

"Yeah, she's in her room." Bobby replied quietly, "I think seeing you would do her the world of good."

"Uh...I...I think I upset her today." Dean said, flushing with guilt and shame, "Just before she left school I told her that perhaps she needed time to breathe, which meant us two spending a little time apart...and I think she thought I was breaking up with her and she just drove away..."

He hung his head and bit his lip, Bobby's gaze softening as he looked at the young boy.

"I...I hurt her, and I'm sorry...I hope I've not disappointed you..." Dean whispered, "I never meant to, I was just thinking about her, and..."

"Dean," Bobby said softly, Dean looking up slowly with tears of shame in his eyes, "I'm sure seeing you will make her feel a lot better, okay? Don't worry. She misunderstood what you meant, that's all."

Dean nodded and Bobby patted his back welcoming him into the house, closing the door and smiling at the boy.

"She's got a vase on her window sill." He said, "It's always got water in it, you can put those in there."

He gestured to the gorgeous bouquet in Dean's hands.

"They're beautiful, Dean."

"I just wanted to tell her I was sorry..." He said, "I saw these in a florist's window on the way from school and I just...I know that lilies are her favourite flowers."

"Very thoughtful of you, Dean." Bobby said with a smile, "I'll get you guys something to drink, alright? Go on up."

Dean began to ascend the stairs, hearing Chrissie's sobs as he approached her room. He bit his lip, taking a deep breath before knocking on the door and entering slowly, watching as the younger teen sat up slowly, blinking in shock as he produced the flowers.

"Hi, sweetie..."

"Dean?" She asked, "W-what are you doing here?"

"I'm here to apologise..." He began, "I didn't...at school I wasn't breaking up with you..."

Chrissie watched as he sat on her bed, letting him take her hand.

"All I meant was that we should perhaps make sure that we spend time together, but also have our own space...y'know? Not breaking up, just not smothering ourselves with each other's company, d'you understand what I mean?"

All Chrissie could do was nod and she took the flowers from Dean as handed them to her.

"I'm sorry I upset you." He whispered, Chrissie grimacing and biting her lip.

"Thank you for the flowers." She said softly, "Don't be sorry, Dean, it was my mistake."

"Chrissie..." Dean began, Chrissie cutting him off with a loving and deep kiss to his lips.

She just hugged him tight and Dean held her back, rubbing her back soothingly as she curled up close to him. He'd hold her for as long as he had to, no matter how long that was.

-TBC-

* * *

**Hope you enjoyed this ridiculously late update! **

**Thanks for reading so far! **

**xxxxxxxxxxxxxx  
**


	4. A Little Time With Me

**Summary: **AU. Dean Winchester and Chrissie Singer are good friends, and during a weekend stay with their friends they grow closer. Dean has to try to cope with falling in love for the first time along with the usual high school drama. Please R&R!

**Disclaimer: **I don't own _Supernatural _or its characters. I only own Chrissie Singer.

* * *

**Love is a Complicated Business**

**~Chapter Four: A Little Time With Me~ **

Dean found it hard not to get upset when he got a text from Chrissie, revealing the news that Bobby was out and she was alone. She needed him, she'd said. She needed someone with her, and he was the first one she'd spoken to.

_Hi, sweetie. My dad's out and I need you. I need someone with me. I'm sorry if I'm disturbing whatever you're doing, but I feel so alone. _

Dean quickly replied, reassuring her that he was on his way to her.

_Don't be sorry, baby, I'm on my way. I'll be at your place in five minutes. _

Chrissie replied with a thank you and much to Dean's dismay he found her sat on the porch steps, her arms wrapped around her knees and her face buried in them as she sobbed quietly. He hated to see her in so much pain, and as much as it frightened him, his deep feelings for her just drew him closer to her with every step, every touch and every kiss.

"Chrissie?"

Chrissie looked up at her boyfriend who took her hands and pulled her to her feet, drawing her close into a protective embrace and kissing her lips with such gentleness it made Chrissie's breath catch in her throat.

"It's okay now." He whispered to her, "It's alright, baby. I promise, I've got you."

She just kept holding him before kissing his lips, sliding their fingers together and leading him inside.

* * *

"Love you too, Dad. Bye."

Chrissie hung up and looked to Dean, sighing and biting her lip.

"He's gonna be away for three weeks." She whispered, her lower lip trembling, "I can't be alone for three weeks, Dean, I just can't..."

"Hey, calm down, okay?" Dean said softly, "I'll stay if it'll make you feel better."

"Y-you will?" Chrissie asked as she began to cry, "You'd do that for me?"

"Of course I would." Dean told her, "I love you, don't I?"

Chrissie's world stopped spinning as those words left Dean's lips, and she stared at him like he'd grown a second head. He loved her. He loved _her _of all people to love. Dean Winchester loved Chrissie Singer. The world had suddenly become ten times brighter.

"You love me?"

Dean, who sat there wide-eyed and dry mouthed, nodded slowly, Chrissie sobbing through happiness before she ran to him, Dean standing up and catching her as she threw herself into his arms, their lips meeting in deep and passionate kisses before Chrissie broke it, cupping Dean's cheeks and stroking them gently as one tear slid down his.

"I love you too." She breathed, "God, Dean, I love you."

They shared a deep kiss, Dean pressing his forehead to hers and nuzzling her gently. They had three weeks together now. Three weeks alone to explore each other and explore the love that they'd found together.

Dean and Chrissie went to the Winchester house for Dean to get his things, including his box of condoms which he kept concealed. He didn't want her to feel uncomfortable or panicked. He'd only brought them just in case they got anywhere. Upon return to the Singer house, Chrissie cooked dinner while Dean took a shower, the two of them sitting down to their meal.

They lay on the couch that night, the firelight casting shadows on the walls around them. Dean held Chrissie in his arms, watching her lift her head and press a kiss to his lips.

"I love you." She whispered, Dean smiling softly and stroking her head gently.

"I love you." He replied, "So much."

* * *

The bedroom was incredibly dark, barely any light coming in through the drawn curtains despite the moon being full and bright. In the beautiful double bed lay two very much in love eighteen year olds, arms around each other, both wide awake. One was thinking of his lover, and the other was thinking of her lover and her recently decided mother.

"What are you thinking about?" Dean asked, stroking Chrissie's hair.

"Nothing much." The young girl lied, "You?"

"Kissing you." Dean whispered, Chrissie resting by his side and cupping his cheek, "I'm thinking about kissing you, right now."

"I'm thinking of kissing you too." Chrissie whispered, the two of them sharing a deep, loving kiss.

The kiss intensified, Dean caressing Chrissie's cheek gently and brushing her hair behind her ear before kissing her again, feeling her begin to roll onto her back. He settled above her, moving over as she parted her legs for him to lay between. They gently kissed and held each other, stroking one another's bodies to explore and feel each other.

Dean leaned into her neck, caressing it softly with his lips as they rolled over so she was on top. Her hands were resting on the bed as he gripped her shoulders and pulled her closer, kissing upward before kissing her chin and suckling for a moment. Chrissie moaned at the sensations, rolling her hips against his as she cupped his face, pulling him up for a kiss before paying attention to his neck in return.

Dean tilted his head to give her more access, moaning quietly at the feel of her lips on his neck. They kissed each other's lips again, Chrissie sitting up and reaching for her vest top, Dean nodding gently as she pulled it over her head to reveal gorgeous, ample breasts, a flat, soft stomach and the beginnings of beautiful hips. Her brown eyes met his green ones, his hands coming up to brush through her auburn curls as he sat up, hands sliding around Chrissie's back.

"No..." She whispered, "Not yet."

Dean pulled back to look into her eyes, noticing that they were tearful. He hated it when they were tearful.

"I'm sorry...I'm not ready."

"Baby, don't get upset." He whispered, "That's okay. It doesn't matter that you're not ready, alright? I'll wait for you. Always."

Damn. He didn't know he could be such a big girl.

"Oh, I love you." She breathed, kissing him and holding onto him, "I love you, Dean."

"Love you too, babe." Dean replied, keeping her held close, "Wanna show you something."

"Oh, yeah?" She asked, a small smile crossing her lips.

"Kneel up."

Chrissie did and Dean kissed her neck, moving down to her shoulders and chest before kissing her breasts gently, feeling her shiver in response.

"Mmm..." She hummed, "Dean..."

"Yeah, baby?"

"More...Please..."

And that was just what Dean gave her.

* * *

Chrissie gripped Dean's bare shoulders, their cotton clad lower bodies grinding together so slowly it was torturous. Chrissie suddenly felt a rush of energy go through her body and she trembled, her muscles clenching as she rode out her first orgasm. The sounds she made, those high pitched, quaking moans and breaths just sent Dean over the edge and he came into his boxers, his body being shocked with the occasional spasm and jolt as they continued to rock against each other. They settled, Dean kissing her lips and laying beside her.

"Love you." He told her, earning a gentle smile in return.

"Love you, Winchester."

Dean smiled softly and took Chrissie into his arms, the darkness making them drowsy as they drifted off to sleep in one another's embrace. To Chrissie this was perfection, laying in the arms of the boy she loved, who happened to love her back. Why he loved her, she didn't know. She didn't feel worthy of his love, however, clearly she was otherwise he wouldn't have told her he loved her. They loved each other, and since her mother's death, this was the first time that Chrissie had been truly happy.

* * *

Chrissie awoke alone. She wondered where Dean was, climbing out of bed and putting her vest top back on to go to the door, just before she reached it, however, it opened, revealing Dean on the other side with a tray of pancakes.

"Oh, you're up..." He said quietly, "Just thought I'd make you..."

"Breakfast in bed!" Chrissie finished with a grin, "Dean, that's so thoughtful, thank you!"

She kissed him lightly and ushered him out of the door.

"Let's try again, huh? I'll get in bed."

She rushed to the bed, climbing back in and pretending to be asleep as Dean entered again, chuckling at the sight before placing the bed tray on the floor and kissing her temple.

"Chrissie?" He whispered, "I've brought you something."

"Oh, Dean, whatever could it be?" Chrissie asked as she faked her wake up, Dean smiling at her and lifting the tray up to which she responded with acting as surprised as she could, "Breakfast in bed? Oh, Dean, you're so sweet!"

With that she kissed him deeply, Dean placing the tray over her legs and watching her tuck into her breakfast.

Yeah, this he could definitely live with.

-TBC-

* * *

**Hope you enjoyed! **

**Thanks for reading so far! **

**xxxxxxxxxxxxxx  
**


End file.
